Hydrochloric Acid → 4-Hydroxy-7-phenoxy-1-phenyl-isoquinoline-3-carboxylic acid methyl ester

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Reaction Conditions

Reaction Steps

A mixture of 1-bromo-4-hydroxy-7-phenoxy-isoquinoline-3-carboxylic acid methyl ester (150 mg, 0.40 mmol), phenylboronic acid (60 mg, 0.48 mmol), Pd(PPh3)4 (46 mg, 0.040 mmol) and Cs2CO3 (261 mg, 0.80 mmol) in DMF (4 mL) was heated at 100° C. for 16 h under N2 atmosphere. After cooling the mixture to r.t., brine (20 mL) and EtOAc (50 mL) were added. 1 M HCl was added with stirring until pH was ˜2. The aqueous layer was extracted with additional EtOAc, and the organic layers were combined, washed with water, and dried over MgSO4. After evaporating the solvent, the crude product was purified by column chromatography (0-25% EtOAc/hexanes+2% AcOH) to give 98 mg of the title compound as a white solid. MS: (+) m/z 372.09 (M+1).

Provenance & Evidence